Structure via PubChem · Public domain (PubChem)
L-topaquinone
Sign in to saveAlso known as (S)-alpha-amino-4-hydroxy-3,6-dioxo-1,4-cyclohexadiene-1-propanoic acid
Topaquinone (TPQ) is a redox cofactor derived from the amino acid tyrosine. Its name derives from 2,4,5-trihydroxyphenylalanine-quinone. Its structure was first identified in 1990. It is used by copper amine oxidases which contain a tyrosine residue near the active site. This residue catalyses its own transition, first to dopaquinone and then to topaquinone, in a Cu2+ dependent manner.
Chemical data
- Formula
- C9H9NO5
- Molecular weight
- 211.17 g/mol
- IUPAC name
- (2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
- SMILES
- C1=C(C(=CC(=O)C1=O)O)C[C@@H](C(=O)O)N
- InChIKey
- YWRFBISQAMHSIX-YFKPBYRVSA-N
- XLogP
- -4.1
- Polar surface area
- 118 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 211.048065
Show 3 more facts
- isomeric SMILES
- C1=C(C(=CC(=O)C1=O)O)C[C@@H](C(=O)O)N
- canonical SMILES
- C1=C(C(=CC(=O)C1=O)O)CC(C(=O)O)N
- chemical formula
- C₉H₉NO₅
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Topaquinone (TPQ) is a redox cofactor derived from the amino acid tyrosine. Its name derives from 2,4,5-trihydroxyphenylalanine-quinone. Its structure was first identified in 1990. It is used by copper amine oxidases which contain a tyrosine residue near the active site. This residue catalyses its own transition, first to dopaquinone and then to topaquinone, in a Cu2+ dependent manner.
== References ==
Excerpted from Wikipedia’s “L-topaquinone” article, available under the CC BY-SA 4.0 licence.